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Synthesis 2009(22): 3797-3802
DOI: 10.1055/s-0029-1217026
DOI: 10.1055/s-0029-1217026
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkA Straightforward Synthesis of (S)-Anabasine via the Catalytic, Enantioselective Vinylogous Mukaiyama-Mannich Reaction
Further Information
Received
19 May 2009
Publication Date:
23 September 2009 (online)
Publication History
Publication Date:
23 September 2009 (online)

Abstract
The tobacco alkaloid (S)-anabasine was synthesized by a straightforward 4-step sequence with the catalytic enantioselective vinylogous Mannich reaction as a key step. Only 3 mol% of a structurally optimized chiral BINOL-based phosphoric acid was employed to control the absolute configuration of the natural product.
Key words
anabasine - piperidine - alkaloids - vinylogous Mannich reaction - Brønsted acid catalysis
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